


First Time

by Emela



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Bottom Derek, Emotional Hurt/Comfort, Feels, M/M, Nervous Derek, Plot What Plot/Porn Without Plot, Porn with Feelings, Praise Kink, Riding, Top Stiles Stilinski
Language: English
Status: Completed
Published: 2015-05-11
Updated: 2015-05-11
Packaged: 2018-03-30 03:54:53
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,998
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3921961
Author URL: https://archiveofourown.org/users/Emela/pseuds/Emela
Summary: <blockquote class="userstuff">
              <p>Derek has all kinds of assumptions about what a gay relationship is like (he’s never been in one after all, and the Internet is not his friend), but Stiles shows him that there’s no rule except one: what makes you happy makes me happy.</p><p>OR</p><p>The one where Derek is nervous about having sex with Stiles, and Stiles is the best boyfriend ever.</p>
            </blockquote>





	First Time

**Author's Note:**

  * For [Lena_221b](https://archiveofourown.org/users/Lena_221b/gifts).



> So, if you've ever read anything I've written before, you might know by now I have a thing about Derek Hale feels during sex. I honestly can't help it. I also think it might be my life's mission to ensure Derek Hale feels love beyond love at the hands of one Stiles Stilinski. 
> 
> For my good friend [ lena221b](http://lena221b.tumblr.com/) who asked for a Sterek fic in which Derek is confused about "tops" and "bottoms" and Stiles fixing it all with his magic cock ;) Also partly inspired by my conversations with the lovely [ cutthissmilefromeartoear](http://cutthissmilefromeartoear.tumblr.com/) who I have very in depth discussions with about Derek Hale feels. 
> 
> I hope you like it Lena! <3

Being with Stiles isn’t hard. Stiles is the easiest thing that has ever happened to Derek, even before they got together.

They fight like they’ve been together for years, they fall asleep on the couch sprawled out on top of each other, nothing awkward the next morning about it. The pizza place they sometimes order from never gives them the correct ratio of toppings and Derek always finds himself picking off all of Stiles’ mushrooms while Stiles steals all of his olives without even so much as a “is this okay?” It just happens, more natural to Derek now than even his routine morning run.

It’s just…the sex.

Sex has always been the problem in every relationship he has had. It’s not the nicest thing to know that every time you thought you were consenting to something it was really just a product of your own naivety and someone else’s manipulation.

Every. Single. Fucking. Time.

Derek knows Stiles is real though. Knows that they are both in this for as long as the universe intends to give them.

Before they happened, Derek always thought if he was given the chance to be with Stiles they would instantly fall into a tangle of limbs on the bed, or the nearest surface, mostly because Stiles is nearly always in a low constant state of arousal and it’s _intoxicating,_ but also because Stiles makes Derek feel like a teenager all over again. It’s nice, and maybe slightly disconcerting, but mostly Derek likes it. Makes him feel like he is getting to re-live something he lost, or never had.

However, when they _did_ finally push past those first awkward _I want to be with you_ confessions, it didn’t go at all like Derek thought it would. Stiles didn’t lurch forward and pull him into a searing kiss. Didn’t instantly push his hand down Derek’s pants or grind against him, moaning “finally” or “we’ve waited too long for this”.

He had just…collapsed on top of Derek and clung to him. Like he thought Derek was going to disappear or something. It was only then that Derek had first realised that he didn’t just want to go slow with Stiles, but he was allowed to. Stiles didn’t demand anything of him, didn’t expect anything of him. He knew about his past. He was the only one who knew, and he gave Derek everything he needed right away without even having to ask.

It has been seven months since they “officially” got together, and Derek would be lying if he said he never thinks about sex with Stiles. He thinks about it _all the time._ Now that he can openly stare at Stiles’ hands and lips without fearing he’ll be caught and found out it’s like he can’t stop.

Derek had never exactly been aware he was into guys before Stiles. In fact, he’s not so certain he _is_ into guys. Just Stiles. He doesn’t know what that makes him, but frankly Derek has never cared about labels. He’s been fighting them his whole life and now all he wants is just to try and be happy, for the first time in a long time feeling like that might actually be a possibility.

Stiles makes him feel like anything is possible sometimes, as clichéd as it sounds.

Sex with women has always come naturally to him, even in his head. He doesn’t know if he’s particularly _good_ at it. The only person who ever praised him was Kate and obviously everything she said was a lie, but even so, it is simple enough. There is one dick and one vagina and tab A goes into slot B, always remember to wear a condom, and the rest his down to, what, chemistry? Experience? Derek has no idea.

Gay sex though. Sex between two men, that hurts Derek’s head. The hand job part he’s fine with. It can’t be much different than masturbating on your own, just from a different angle, and blow jobs don’t unnerve him. Sure he’s never given one, and even though he knows Stiles isn’t a particularly patient person, Derek imagines he’ll be just as good a teacher in bed as he is in getting the pack learned up on just about everything. Plus, the thought of Stiles’ lips wrapped around _his_ cock is one he is very much looking forward to being a reality. No, what worries him is the anal stuff.

He’s heard of Tops and Bottoms before. He knows there’s got to be prepping involved even if he has never touched himself _there_ before. It’s always felt too strange, and after Kate Derek has never felt much like experimenting. He wants to be a good boyfriend though. He wants to give Stiles back everything he has given him and show him waiting until he was ready was worth it.

It’s just…it’s not like you can just go and buy a book on how to have gay sex. Well, Derek is sure there _are_ books out there that exist on the subject, but he’s too embarrassed to go hunting for them and he _definitely_ doesn’t want to order one, especially when the pack now uses his loft as a second home and would undoubtedly open any packages Derek got delivered. He will never hear the end of it, especially if Erica is the one to find it.

So that leaves the internet.

Porn, as it turns out, is not everything he thought it was going to be. There might have been a time where Derek got turned on by two people he doesn’t know getting all hot and bothered, but in all honesty Derek thinks he prefers love scenes in movies. He likes the build-up and getting to know the people, as far as one can through a television screen, and porn definitely doesn’t give him that. Maybe if he watched it with Stiles it would be different. Maybe even hot. By himself, however, not so much.

He does quickly come to realise a common theme in a lot of the videos though. The bigger guy is always on top, whereas the smaller of the two is always on the bottom. Derek doesn’t know how the rules apply to people of equal body mass, but since he and Stiles _are_ different body types he supposes this is what Stiles expects to happen between them.

Does that mean Stiles assumes Derek will know what to do as a Top?

He looks into it further and finds some stuff on lube, water versus oil based, and the suggestion he may want to wear gloves which just serves to make him freak out a little because he _knows_ Stiles will, you know, prepare himself or whatever, but part of him still wonders if he has to ask. Bring out the gloves and actually ask Stiles if he should wear them. The thought alone is just all kinds of embarrassing and the least romantic thing Derek can think of for a first time.

In all honesty, Derek would much rather Stiles be on top, at least the first time, but whenever Stiles has teased him with dirty talk during their- very heated to the point Derek gets light headed- make out sessions he always talks about _being_ fucked. Not once has Stiles ever mentioned doing the fucking. It makes Derek a little sad, because he’s curious about what it would feel like, having a dick inside him. But he guesses that’s not something common to want amongst guys like him. Maybe he’s just as fucked up in this aspect of his life as he is in everything else.

It doesn’t surprise him. Of course he would be the only Top wanting to Bottom. Of course.

Still, being with Stiles in any capacity is all Derek really wants and so he sits patiently through videos of guys being opened up, takes note of how long they all take, winces at the ones who don’t use enough lube or are quick to go straight to using their dick after only one finger. Derek will definitely not do that to Stiles. He’s not exactly small and the thought of not preparing Stiles enough makes him shudder. He’s going to make this _good_ for Stiles. In the end that’s all that matters to him.

So he goes out and buys all the stuff. Lube. Five different kinds, scented and unscented. Condoms, even though werewolves can’t catch or transmit diseases. Plus, he doesn’t know if Stiles will like the idea of him coming inside him, and better safe than sorry, right? He even buys a pair of latex gloves _just in case,_ although he really hopes he won’t have to use them, that Stiles will do what he does best and let his mouth run away with him and tell Derek how he has showered _very thoroughly,_ maybe with an added wink to diffuse any awkwardness.

Derek is pretty sure Stiles could diffuse a war with that wink of his. It makes Derek’s whole body go lax and hot at the same time. Derek doesn’t know if that’s even normal, but he’s willing to go with it because Stiles makes him feel…just makes him _feel_ period. Good. Alive.

Wanted.

Derek can’t remember the last time he felt wanted until Stiles came along. It is entirely confusing, something Derek still can’t quite accept, but he’s working on it. _Stiles_ is working on it.

Derek kits the loft out in candles. He decides lots blankets and pillows on the floor are more romantic than his bed. At least the lounge has a window and a view, if nothing else. His bedroom is pretty barren as far as bedrooms go. Stiles constantly teases him with the threat of IKEA trips and potted plants, but Derek has a feeling an IKEA trip with Stiles would be far more likely to result in buying different kinds of ice cube moulds than items of decoration, or anything remotely practical.

He wants to say he doesn’t know why he’s so nervous, that he shouldn’t be nervous, but he is. He does. He feels like his stomach is just one big roll of toilet paper and someone is yanking on it furiously, unravelling it and making him feel dizzy, making him want to throw up.

The whole thing makes his vision go fuzzy and he doesn’t even notice he’s having a panic attack until he’s sitting between Stiles’ legs on the floor, back cradled to his chest.

“Shh,” Stiles soothes. “I’m here. It’s okay. I’ve got you.”

Derek nods, tears stinging his eyes because he’s already fucked this up. There isn’t one thing he can do right on his own, not even making love to his own boyfriend.

“I’m sorry,” Derek chokes out, pulling away. Stiles lets him get as far as standing up before he’s back in his space, arms around his waist and placing kisses all over his face.

“Hey, none of that. What happened?”

“I- I…” Derek doesn’t know what to say. _I don’t know how to have a relationship? I don’t know what I am doing? I’m scared I’m failing you?_ He wants to say all of these things, but somewhere inside him he knows Stiles already knows them, and what comes out instead is, “I don’t want to top.”

“Excuse me?” Stiles asks.

Derek takes a deep breath and shuts his eyes.

“I don’t want to top. At least, not right now. I just want…Stiles I’m so sorry. I know I’m supposed to be the one who…you know…but it’s too much and I’m afraid of hurting you and not doing it right and-”

“Whoa, whoa,” Stiles says, cutting him off with a kiss. “What do you mean _supposed to_? Derek you do know just because you’re my big muscly sourwolf doesn’t mean you have to top, right? _Right?_ Oh my god,” he sighs when Derek refuses to look up at him. “Derek, no. Just…no. You should have told me! Is that what you’re freaking out about? Supposed to? Fuck, I am so stupid. I just assumed- I never thought you’d let me- _stupid, Stilinski, stupid._ ”

Derek smiles despite himself, unable to help it whenever Stiles starts muttering to himself. Derek doesn’t think Stiles even realises he does it and Derek plans on never telling him, doesn’t want to risk Stiles stopping doing it by becoming aware of it.

“Okay, new rule. We talk about everything. _Everything._ I don’t care if you have to start writing a diary and just leave it sitting out for me to read, but you mean the world to me Derek and I’ll be damned if I don’t do everything in my power to make you happy!”

Derek frowns, unsure what to do with that. Logically he knows Stiles wants to make him happy. That’s what good boyfriends do and Stiles is a damn good boyfriend, but he still doesn’t understand, not really, how this kid with the majestic brown eyes and wickedly smart brain, this kid who is both funny and loyal, _this kid who found something worth fighting for in him,_ can possibly care so much if he is happy or not.

It doesn’t compute in his mind, and maybe that makes him broken or maybe it just makes him wise, not getting his hopes up that Stiles really will want this forever, but either way it sucks. He doesn’t want to feel this way; surprised every time Stiles so much as brings him take-out, detached in a way that doesn’t even feel lonely, just…fragmented. Like bits of him are missing, floating in front of him and every time Stiles is with him those bits fall back into place, pressed back into him with the weight of his body against his, a reassuring presence. And yet, when he leaves, those pieces never stay. Sometimes he thinks it doesn’t matter he can’t hold himself together when Stiles can do it so easily for him, but then he thinks of all those _what ifs._ What if Stiles leaves him. What if something happens and Derek is left without him? What if he finds someone better, younger?

He knows he shouldn’t think like that, but that doesn’t mean he can help it.

“I know what you’re thinking, big guy,” Stiles shakes his head fondly, exasperated, taking Derek’s hand and intertwining their fingers.

Derek raise his eyebrows in an _oh, really?_ despite having no doubt Stiles knows _exactly_ everything he is thinking. Sometimes it feels like Stiles has access to all of his thoughts and memories. It scares him, but it also means Derek doesn’t have to say much to get Stiles to understand him. Sometimes he just moves in a certain way and Stiles knows whether he needs a cuddle session or what Stiles has come to call “the Stilinski distraction” which usually consists of Stiles picking up the nearest book to hand and reading it out in funny voices in an endless attempt to make Derek laugh. (Derek pointedly does not think of how good Stiles would be if they ever had kids. Pups.)

Derek can easily imagine how amazing a Dad Stiles would make. Sure, he would most likely join in with the kids in messing up the house rather than scolding them for it, but he’d love them fiercely, werewolf or not. Protect them and relish in finally getting to do the whole “I have a gun” routine the Sheriff pulled on Derek when they first got together on anyone they dated.

“You’re scared you aren’t enough,” Stiles whispers, pulling Derek back to the present, away from a future he’s already terrified of losing.

“Well, I’ve got something to tell you, Derek Hale. You are. I know you aren’t going to understand this because I see the way you look at me sometimes. Like I’ve saved you or something, Superman style.” He rolls his eyes. “But the thing is Derek, I’m stubborn. I don’t have a tragic past that warrants me any sympathy, okay? I lost my mom, but so have a lot of people. I’m human, I involve myself in all of this, but I’m not forced into it. I could leave, I’m not bound by anything that going wouldn’t solve. You’re the one with the bad guy’s back story, Derek. You’re the one who got back up in spite of it and became the hero instead. Because _you are a fucking hero._ You could have easily been what Jennifer was, but you aren’t. Don’t scoff at me, it’s true! I’m the kid who actually _became_ the villain for a while and I don’t know how to deal with that. I know it wasn’t me, but I remember it. I remember everything and sometimes I feel like I’ll go out of my mind with the memories. Sometimes something as small as a fly in my room triggers it, and I want to call someone to help me, but I can’t bring myself to. I want to make it out on my own, so I you know what I do? I think of you. I think of you and what you’ve been through and what you are, how you grew to be good and kind even though life dealt you the shittiest hand imaginable. I think about how much you care for this pack, even though you struggle to show it. How even after everything you still took one final chance on love and let me in. Derek…you’re…you’re just everything and that’s why you can be sure you are enough.” Stiles takes his face in his hands. “That I will never leave. I’m young, but I’m tied to you, and not in a way where one day I am looking down and I find I’m tied to you without knowing how it happened, but in a way where I watch myself physically tying the knot. I tie it over and over every day because I can’t imagine a life without you and I don’t care how cliché that sounds.”

“Stiles, I-” What is Derek supposed to say to that? What is he-

“Don’t cry, sourwolf,” Stiles whispers, tracing his thumbs across both of Derek’s cheeks. “Please, really don’t. If you start, I’ll start and then instead of the sexy times I am hoping will still happen, even if just in the form of dry humping, we will end up eating ice-cream and watching one of those sappy romantic comedies we both secretly love but refuse to admit we do.”

Derek laughs, his nose running, the tears still coming and he doesn’t know why but the moment Stiles take his shirt- his favourite plaid shirt- to wipe at Derek’s nose is the moment everything comes to a stop for him, the moment it all clicks.

Clicks that Stiles _loves_ him. Really, I don’t care how disgusting you look I will still look at you like you’re my whole world, loves him.

For a second Derek can’t breathe and then his lips are on Stiles, kissing him everywhere he can reach.

“Did you just wipe my nose?” he huffs against him, an easy smile catching him off guard.

“Don’t make a big deal out of it,” Stiles says, pulling back and rolling his eyes. “It was instinct.”

“Instinct,” Derek repeats, smile faltering, heart constricting. “That’s never- no-one has ever…not since my family…”

Stiles smiles sadly, but it isn’t pitying and he reaches out and winds his arms around Derek’s neck, pulling him in until their foreheads are touching.

“I know I’m not the right type of family for you,” he whispers. “I know you don’t have with me what you had with them, unconditional love, they type only a parent can have for you. Blood.” He sighs, and Derek knows Stiles is thinking about his mom. Derek wishes it isn’t something Stiles has to live with every day. He knows Stiles blames himself for it, just like Derek blames himself. But that’s the thing, isn’t it? That’s part of the reason why Stiles understands him so well.

“But the thing is, Derek,” Stiles goes on, sliding one hand down Derek’s chest until it’s resting above his heart. “It would be pretty foolish of me to take a bullet for you given I can’t heal and you can. Most of the time it’s going to be you saving me, unless you’re already out cold and you require these babies to slap you back to consciousness.” He wiggles his fingers and forces a laugh. “I’m great with plans and I’ve got a pretty awesome relationship going on with my bat-“ he smiles- “but I know that’s how it’s going to be and, yeah, so that kills me a little, knowing I can’t jump in front of you, but you can be damn sure I’ll always run back for you. I’ll never think about it even for a second, Derek. Wherever you are, I’ll be, and that’s not some cheesy line from a movie, some grand gesture that I never think I’ll really have to live up to. That’s just a fact. I’ll follow you wherever you go. You’ll spend your life bandaging me up and I’ll spend mine protecting this.” His hand clenches around the material covering Derek’s heart before it slips down and pulls his t-shirt up, and then Stiles’ lips are right there on his skin, breathing gently, kissing softly.

“I know you’ve ever only had one relationship that wasn’t toxic, when you were still young enough to take chances and not be afraid of getting hurt. I know placing your trust in me must be terrifying. I know how easy you think it would be for me to stop loving you, but the thought of not being with you…” he snorts. “I know all that stuff on mates isn’t real, but I feel I’ve already loved you for so long, like my fucking soul has known yours for a thousand years.” He laughs and shakes his head, tickling Derek’s chest with his hair before bringing it back up so amber eyes are searching his.

“I know movies teach us young love doesn’t last and that people who jump into relationships before they’re twenty-one are more likely to realise what they once thought they wanted isn’t what they turn out to want by the time they’re forty, but I call bullshit. I wouldn’t be with you now if I wasn’t sure, Derek. I know what I’m getting into when I tell you I love you. I’m telling you forever. I’m telling you I know we’ll survive the fights and the pain. I’m telling you I’ll never not want to spoon with you every night, or wake up to you every morning. I’m telling you I want lazy sex and intense looking-into-each-others-eyes sex. I want we-didn’t-die-today sex. I want we-haven’t-had-proper-sex-in-a-week-because-the-kids-refuse-to-sleep-in-their-own-bed sex. If kids are something you want. If that’s something you still think about. I don’t care. As long as I get you, I don’t care what else life gives me. You’re always going to be the most important to me, so, yeah. _Boom._ Deal with it, buddy!”

Stiles is fidgeting slightly now, eyes darting between Derek’s face and everywhere else in the room. Derek wants to respond. Truly he does, but he’s never been good with words and maybe one day he’ll learn to be. Maybe one day Stiles’ incessant talking will rub off on him, but for now all he can do is lean into Stiles and fucking _hold on,_ pushing him down until they are both lying side by side on the blankets Derek laid out for them.

Derek is still nervous, feeling like a virgin all over again, but with Stiles’ hands on him, petting and caressing, he knows it’s all okay. That’s he’s safe.

“What do you want to do?” Stiles asks, running his fingers through Derek’s hair.

“Everything,” Derek breathes.

Stiles chuckles.

“Maybe not all at once, big guy, but we’ll get there.” He winks and Derek flushes, not with embarrassment but with heat. With want, all for this boy with the ridiculous whiskey eyes and expressive can’t-stay-still-even-for-a-moment hands. For this _man_ who saves him, without who they would all be screwed, possibly even dead. Derek knows he would be.

“I want to get undressed and maybe kiss a little more,” Derek offers then, shyly. Yes, that’s exactly what he wants, and if they way Stiles smiles is anything to go by he’s more than happy to go with it.

He reaches out for the hem of Derek’s t-shirt then, but Derek stops him.

“I know you’ve seen me naked before,” he says. “But…” He frowns, unsure how to explain.

“But it’s a big deal now?” Stiles finishes for him. Derek nods and looks away, hating himself for finding it this so hard. He supposes he has every reason to find sex difficult, but this is so much more than sex. With Stiles it’s fucking _making-love_ and Derek’s never had that before. He’s never done slow. He doesn’t know what to do when it’s not just about chasing an orgasm, but actually _being with someone._

“Stop thinking,” Stiles says. “I do too much of that already. Here,” he places a kiss to Derek’s forehead. “Stand up for me, I have an idea.”

Derek does as Stiles asks and watches as Stiles goes to stand at the opposite side of the blankets from him.

“Me first,” he says, unbuttoning his shirt and letting it slide off of his shoulders, revealing a pale, mole littered chest and two, rosy pink nipples. Stiles isn’t by any degree muscled, but he isn’t as skinny as his choice of clothing always makes him out to be. He’s toned and perfect and everything Derek couldn’t have hoped to imagine before now.

“Your turn,” Stiles says, giving Derek an encouraging smile.

Derek doesn’t know whether to pull his t-shirt off quickly, it would be easy to just whip it off, but he finds himself going slow. Not a strip-tease or anything- Derek doesn’t even know how to even do that- but taking his time, giving himself a few extra moments to breathe, the scent of Stiles even from across the room settling him.

Once his t-shirt is on the floor, he can’t help but smile at the way Stiles’ heartrate picks up. He knows Stiles has seen him a hundred times like this- Stiles actually keeps extra t-shirts in his jeep now because Derek loses his so much to blood and claws and whatever else they’re hunting down- but it still warms something inside him to know Stiles hasn’t become used to it, that it’s all still a big deal to him.

“Okay,” Stiles whispers, moving his hands to the front of his jeans and popping the button there. He pauses then, just for a moment, before gripping the waist band and pulling the material down, stepping out of them one leg at a time, removing his shoes and socks too, and throwing everything away somewhere across the room, but Derek’s doesn’t see where, too entranced by strong legs and creamy, lightly furred thighs.

Derek nods, blinking once, maybe several times, his mouth turning slightly dry, before copying the action, leaving them both standing across from each other in nothing more than their underwear.

“Ready?” Stiles asks, beginning to inch down his boxers.

Derek doesn’t trust himself to speak, so he just nods, hoping that’s enough.

It is, and then Stiles is naked. Naked and _his_ and Derek takes a step forward, wanting to touch. God, he’s beautiful. So fucking beautiful, cock hardening gracefully- can a cock even _be_ graceful?- the more Derek stares at him.

“Come on,” Stiles whines, folding his arms across his chest and nodding in Derek’s general direction. “I’m two seconds from running over there and ripping them off myself.”

Derek laughs, feeling the last bit of tension drain out of him at Stiles’ impatience.

He doesn’t look at Stiles when he sheds that last bit of clothing, just takes his boxers off and kneels down on the blankets, waiting.

Stiles is on him in an instant, kissing and touching him everywhere and Derek leans into it, kissing and touching back, unable to get enough, words like _finally_ and _oh god_ and _right_ chanting in his head.

They end up lying down in the same position as they were before, just exploring with their hands and mouths, saying nothing whilst exchanging the briefest of kisses, their breathing maybe just a little shaky as they press closer and closer together.

“I can’t believe we got here,” Stiles says, running a hand down Derek’s back. “Did you ever think we’d get here?”

“No,” Derek replies truthfully. “I didn't want to hope, ever since that day you told me I wasn’t a...an abomination. I thought, but I didn’t…” he trails off.

“I’m sorry it took me so long to get there,” Stiles whispers, fingers tracing lower until they are brushing over Derek’s ass. It’s intimate, but not entirely sexual and Derek relishes in it, being touched in that way; a way that isn’t demanding, or wanting, but content, _right._ Like he’s precious or something.

“I ignored it for so long,” Stiles continues. “But that night, when we went after Scott and you were lying there…”- he shakes his head, as though trying to clear it- “Derek, I didn’t know what to do. It was the moment I finally _got it_ and you were sending me away, and I thought my heart was going to beat right out of my chest. I kept telling myself I needed to get to Scott and everyone was leaving and I was so angry they did. I kept turning back, trying to memorise your face, like if I looked at it long enough, if I just held onto it you wouldn’t die.” He swallows, and Derek can hear the lump there, the sudden tears he is trying to fight.

Stiles has never told him that before and interlacing their fingers, Derek tries to get him back to the present.

“Hey,” he whispers. “That’s all the in the past now.”

Stiles’ eyes flick up to his.

“Doesn’t always feel like it,” he says.

Derek frowns, once again berating himself for not knowing what to say. But he thinks Stiles gets it though when he leans in and kisses him, pulling him on top of him and wrapping one leg around his waist, wanting him impossibly closer.

“Alright,” Stiles laughs quietly into his mouth when Derek takes both his hands and pulls him taut over him, flush against him. “I get it. Here and now.” He grinds down with his hips then, a full on body roll that’s totally at odds with Stiles’ usually uncoordinated movements, grinning through a moan when Derek curses at the fire beginning to lick its way up his body.

“Feel good?” Stiles asks, leaning down to kiss Derek’s neck, sucking a bruise there even though it can’t last. Derek wishes more than anything Stiles could mark him, but as Stiles moves to suck another mark further down just above his collar bone he finds it doesn’t really matter because some part of him knows Stiles will never stop trying to leave marks. Maybe one day he’ll spend hours doing it, just marking Derek up and watching his work disappear, doing it all over again. Maybe Derek could find a way to slow the healing process, just for a few days.

“Yeah,” Derek breathes. “So good.”

“Want to feel even better?” Stiles asks, waggling his eyebrows, breaking one hand free of Derek’s hold to trace long fingers down his body, leaving a different kind fire in their wake, until they come to rest on Derek’s thigh behind him. “I’ll make you feel so good, Der. I promise.”

Derek believes him, can’t think of a reason to doubt him, and taking a deep breath he lets his legs fall open as Stiles begins to work his way down his body, placing kisses everywhere he can reach.

“Hips up for me,” he whispers. Derek does as he’s told and Stiles slides a pillow under him, taking a hold of Derek’s calves and stroking them before slowly pushing them forward.

“It would probably be easier to do this on your hands and knees your first time,” Stiles says. “But I have a feeling it might be better for you to be able to see me. I know it doesn’t make much of a difference, but-”

“No,” Derek cuts him off. “Seeing your face- I- I’d prefer that.”

Stiles nods, smiling, but his eyes are serious, watching Derek carefully.

“If I do anything that doesn’t feel good, tell me. That’s not up for discussion.” He lets go of Derek’s legs then, trusting him to keep them in place while he comes to hover over his body, climbing on top of him until his hands are placed on either side of Derek’s face. “I mean it, Derek. I won’t care if you want to back out, if this feels too soon or too much at any time. Even if it looks like I am _just_ about to come. I won’t give a fuck.”

Stiles heartbeat remains steady as he says it, and it might be stupid, but knowing Stiles is giving him that means the world to him. There had been times when it had been too much with Kate. Derek had asked to stop, embarrassed to ask in the first place, but she always ignored him, quietening him with kisses as she continued to take what she wanted. Derek always became distracted by the kisses. They were so uncommon and Derek craved them, craved them so much he just let Kate do whatever pleased her as long as he was under their attention.

But Stiles isn’t Kate and Derek lets himself trust that even at the last moment Stiles would pull out and throw himself across the room before continuing doing anything Derek can’t handle.

“I’ll tell you,” he says, smiling, gaining a small, private smile from Stiles in return.

“Okay,” Stiles whispers. “Do you have lube?”

Derek blushes and points shyly behind him. Stiles looks up past his head and Derek can tell the moment he sees all the bottles by the way he bites his lip, presumably keeping in a laugh.

“How much sex did you think we were going to have?” he asks, eyes wide, leaning over to grab all five bottles, inspecting them.

“I didn’t know what was best,” Derek admits, stealing a nervous glance at Stiles’ face.

“You certainly didn’t go cheap,” Stiles says, lips pursing, looking impressed. “I’m glad you only bought one oil based one. I don’t like them,” he says, throwing that to one side. “ _These,_ on the other hand,” Stiles looks up at him and dramatically clutches his chest. “You’ve truly spoiled me. I’m touched.”

Derek rolls his eyes, despite how his cheeks heat further up. Stiles doesn’t seem to care he has no clue what’s he’s doing though, and that makes something settle inside him, making him bold enough to pull his legs closer to chest, exposing himself fully to Stiles.

Stiles almost chokes when he registers the action.

“Okay,” he breathes out. “I’ll look at the scents later. Plain old unscented it is!” He opens the cap and Derek groans when he hears the liquid coating Stiles fingers, unable to see from his position on the floor, but he can imagine it well enough.

The first finger is a bit of a shock, cold, and Derek jerks slightly, but Stiles crawls in between his legs and kisses his knee, soothing him.

“We’ll go slowly, okay?”

Derek nods and closes his eyes. He wants to look at Stiles, but it’s comfier to just let his head settle back and he smiles, realising this is the first time he has trusted someone enough not to look at them the whole time, to see what they are doing. Watching someone has never been a sexy thing for Derek, always more rooted in fear than anything else. Not trusting his werewolf senses enough to be able to detect if he’s in danger of being hurt.

“I’ve got you,” Stiles whispers, and then a finger is tracing his hole again, teasing, and begging for entrance. Derek doesn’t know if there is something he’s supposed to do to let Stiles in and he tries to push down, hoping to force it, but Stiles backs off immediately.

“You’re so perfect, but let me, okay? It might be a bit weird at first, but I’ll make it awesome. I’ll make it so awesome it will be all you ever think about.”

“It’s just…I’ve never. Not even myself. I-”

“Shh, I know,” Stiles says. Derek doesn’t know _how_ he knows, but he’s Stiles so of course he does. Just like he knows everything. “Thank you for giving me this,” he adds, so softly Derek doesn’t think he is meant to hear. If he was human, he wouldn’t have.

Derek tries to relax then, letting Stiles massage his rim, sucking in a shaky breath when his finger slips past and, okay, it does feel weird, but it also feels good. Fuck, does it feel good. He never doubted Stiles when he said it would, but somehow he had just thought… _fuck._

“More,” Derek pleads. “Stiles, please, I can take more.”

“Gonna fill you up,” Stiles whispers, taking his time before adding another. “You’re doing so good, sweetheart.”

Derek wants to laugh at the endearment, it feels so unnatural between them. In all honesty, Derek has never been one for them. He cringes when he hears “babe” or “baby”, hates “honey” and “darling”, but coming from Stiles it’s a little different. Maybe because Stiles isn’t saying it to be cute, but just because.

Stiles does something with his fingers then, moves them in a way that makes Derek moan, but it’s nothing compared to when they sink deeper and brush something that sends his whole body rigid, spine arching off the ground as he cries out with how amazing it feels.

Stiles makes an appreciative sound and moves closer, planting kisses anywhere and everywhere as he finally adds a third finger. It’s a bit of a stretch, but the burn fades to pleasure fast and Derek feels so _full,_ but it’s not enough. Not nearly enough.

“Stiles,” he whimpers. “ _Stiles._ ”

“Shhh,” Stiles soothes, brushing over that part of him again, his prostate Derek imagines, that makes him see stars. “Just a little longer. I know you’d heal, but that doesn’t mean I want you to have to.”

Derek nods, understanding, but he can’t help pushing down onto Stiles’ fingers anyway, wanting to feel more of him. God, he’s never felt this good before. Sex has never felt bad, per se, but it’s never been like this. He feels cherished and loved, like he’s worth taking the time over, and the thought makes something funny turns inside him, but when he hears Stiles gasp when he clenches around him, trying to draw him in further, he doesn’t care, forgets all about everything before right now.

“You’re so beautiful like this,” Stiles says. “I mean, you’re always gorgeous. You could be a supermodel if you wanted, but _god,_ Derek.” He makes a strangled noise. “I’m so close and I’ve not even touched myself yet.”

Derek opens his eyes then, looking down to where Stiles’ cock is hard and leaking pre-cum. Derek licks his lips instinctively, wanting to taste, but then Stiles is removing his fingers and Derek _whines_ at the loss, hole fluttering around nothing.

“Empty,” he mouths when Stiles comes to lean over him again.

“I know, sweetheart, I know, but I’m going to take care of you.” He kisses Derek then, a long, deep kiss that leaves Derek feeling dizzy.

“You can if you want, but…maybe don’t use a condom?” Derek asks hopefully when they break. He wants Stiles to come in him so badly, wants to be full in every sense of the word and he tries desperately to convey that with his eyes, searching every inch of Stiles’ face pleadingly.

“Are you sure?” Stiles asks. Derek nods, maybe a little too enthusiastically, like an eager puppy or something, but if it gets Stiles in him faster he really doesn’t give a fuck how he comes off.

Stiles smiles, bright and beautiful in that way he doesn’t realise he does and cups Derek’s face.

“I was thinking,” he says, biting his lip. “Maybe you could ride me?”

Derek’s eyes widen at that, cock spurting pre-cum at the thought of Stiles being under him, of being able to bury his face in Stiles’ neck.

Derek is always careful about scenting Stiles, especially his neck. The neck is a big deal to born wolves, and Derek could spend hours sniffing Stiles’ neck, pale and beautiful, his scent strongest there, his pulse point alive and vibrant with energy, just like Stiles himself. Stiles knows what it means to Derek, offers his neck up freely often, but Derek rarely takes the opportunity, not ready to immerse himself, his wolf, with such an intimate part of Stiles yet. But now…now it’s too much to resist with the thought of Stiles buried deep inside of him.

“Yes,” Derek whispers. “Please.”

Stiles grins and getting a hand under Derek rolls them both over with a strength Derek really shouldn’t be surprised at any more.

“I’m all yours,” he says, partly teasing, partly wide-eyed, waiting. Maybe even just a tad nervous too, and when Derek climbs on top of him, Stiles’ whole body begins to shake.

Derek doesn’t really know what to do to soothe him and settles for running his hands up and down his sides and playfully taking his lower lip in his teeth, growling.

It makes Stiles laugh and Derek preens, oddly proud of himself even though he makes Stiles laugh all the time. (Not intentionally, usually, but it’s a thing that happens.)

“You good?” Stiles asks, reaching out to slick himself up with more lube. Derek nods, mesmerised slightly by Stiles’ cock. It’s just an ordinary cock, Derek knows. There’s nothing particularly beautiful about it, but god it is nice to look at.

“Lift yourself up a bit for me,” Stiles whispers. Derek does as Stiles asks and Stiles places a steadying hand on his hip, caressing him, before guiding Derek back down to where he has positioned his cock under him.

Derek’s eyes roll back in his head as the tip breaches him, hands scrambling to clutch at Stiles’ chest as he continues to lower himself down until he’s fully seated.

“Stiles,” he gasps. He wants- fuck, he doesn’t know what he wants.

“Nice and slow,” Stiles says, moving both hands to grip Derek’s waist, holding him. “Take as much as you want.”

Derek’s eyes travel over to Stiles’ face, needing to see him as he lifts himself up, nearly all the way off, before falling back down again, practically sobbing when the movement brings Stiles’ cock in contact with his prostate.

“That’s it,” Stiles gasps, sounding as fucked out and broken as Derek feels. “Good boy.”

Derek whimpers at that, not used to praise, and raises himself up again, coming down harder this time, making them both cry out.

“Oh god,” Stiles moans. “Derek. _Derek._ ”

Derek murmurs something incoherent in agreement, he has no idea what, but Stiles’ hips buck up in response, fucking into him and _oh_ that’s a whole different kind of good.

“Stiles, I want- want to be closer.”

“Pretty sure this is as close as it gets, big guy.”

Derek shakes his head, determined, and lifts all the way off this time, pulling Stiles up with him before climbing into his lap.

“Like this?” Stiles asks against Derek’s mouth, licking along the seam until Derek parts for him and allows his tongue inside.

“Please,” Derek whispers, moaning as the kiss deepens, feeling himself shake a little as Stiles guides him down once more, filling him up and _yes,_ this is so much better. This is what he needs _._

Without wasting another second more, Derek buries his face in Stiles’ neck and inhales deeply, sighing happily as Stiles’ earthy scent fills his nostrils.

Stiles half laughs, half moans in response and sliding two hands under Derek, cupping his ass, encourages Derek to move a little more.

Derek doesn’t lift his head as he begins to fuck himself on Stiles’ cock in earnest, taking everything he can and basking in the moans that fall from Stiles’ lips and fill the room, bouncing off the walls. He always knew Stiles would be vocal, but he preens even further in the knowledge that it’s him that’s causing it.

“Love you so much, Der,” Stiles whispers against him, kissing the hollow of his neck. “Fuck, do I love you. Scares me sometimes how much.”

Derek makes some kind of sound, trying to make Stiles understand he feels the same, but unable to articulate it. Instead, he clenches around him, biting down gently on the pale column of his neck as he feels that familiar pull in his groin. It feels like he’s been waiting forever to come, and although he wants to, wants to so badly, he wants Stiles to come more. Just wants to be filled by him, marked inside when he can’t be outside. Other wolves would be able to smell it, he thinks briefly, would be able to tell he belongs to Stiles, and more pre-cum dribbles down his cock just from the thought alone.

“Want me to touch you?” Stiles asks.

Derek shakes his head.

“Want to come like this.”

“Shit, Derek. You’re going to kill me,” Stiles groans. “Gonna come untouched for me?”

“Yes,” Derek gasps, Stiles meeting him thrust for thrust now, hitting his prostate every time. “Like a good boy.” Derek will feel embarrassed about saying that later, but right now that’s all he wants. Wants Stiles to see him as a good boy, just wants to feel like he’s getting something fucking right for once.

“My good boy,” Stiles whispers. “Always,” and then Stiles’ fingers drift down to the cleft of his ass, where they both meet and Derek just loses it, his orgasm taking him by surprise, spilling between them and crying out Stiles’ name, unable to stop saying it as Stiles fucks him through the after-shocks, taking a hold of his cock and milking him for all he’s worth.

Oversensitive, but not ready for Stiles to stop touching him yet, Derek bites down on Stiles’ neck to muffle his whimpers, and apparently that’s all it takes to send Stiles tumbling over the edge too, hips faltering as he comes on a silent moan, pumping hot and wet inside him, fingers digging into Derek’s ass, hard enough to leave bruises if he was human.

Derek doesn’t know how long they stay like that, breathing heavily, Stiles more silent than he has ever been as long as Derek has known him. It’s nice, but Derek wants to hear- needs to hear- Stiles’ voice and begins to nuzzle the side of his face, hoping he understands.

“Sourwolf,” Stiles whispers into his skin, and Derek grins at the sound of his old nickname, said so reverently.

“When did that become something you call me out of fondness?”

“Was always fond,” Stiles mumbles, pulling back slightly and kissing Derek on the mouth. “I don’t give those kind of nicknames to just anyone you know.”

Derek’s heart flutters stupidly at that.

“Stiles?” he says.

“Yes?” Stiles searches his eyes, holding them like he can’t bear to stop looking.

“Thank-you for, you know, you.” It’s the closest he can come to saying those three words; the ones that roll so easily off of Stiles’ tongue, even though Derek knows it’s still a big deal for Stiles to say them too.

Stiles shakes his head, smiling.

“You too,” he whispers. “Always.”

**Author's Note:**

> My [ tumblr](http://pale-silver-comb.tumblr.com/) where you should come and talk to me about all the ways in which Derek Hale needs to be loved!


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